Abstract
Neothramycin has been isolated from Streptomyces MC916-C4 in the laboratory of Dr. Hamao Umezawa(Takeuchi et al., 1976). It is a potent antitumor antibiotic of the pyrrolo(l,4)benzodiazepine group, which anthramycin (cf. a review by, Kohn, 1975), sibiromycin (see a review by Gause, 1975), tomaymycin (Arimaet al., 1972) and mazethramycin (Kunimotoet al., 1980) belong to. Neothramycin1 contains two stereoisomers A and B in nearly equal amounts. The structural elucidation and total synthesis have been reported by Miyamoto et al. (1977). Both antibiotics are hydrated within 60 min after being dissolved in water, forming the 10-hydro-ll-hydroxyl-derivatives (Fig. 1). The hydroxyl groups at C-3 and C-ll epimerize in aqueous solution.
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References
Arima K, Kohsaka M, Tamura G, Imanaka H, Sakai H (1972) Studies 011 tomaymycin, a new antibiotic. I. Isolation and properties of tomaymycin. J Antibiot (Tokyo) 24: 437–444
Gause GF (1975) Sibiromycin. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 269–273. Springer, Berlin Heidelberg New York
Hisamatsu T, Uchida S, Takeuchi T, Ishizuka M, Umezawa H (1980) Antitumor effect of a new antibiotic, neothramycin. Gann 71: 308–312
Hurley LH (1977) Pyrrolo(l,4)benzodiazepine antitumor antibiotics. Comparative aspects of anthramycin, tomaymycin and sibiromycin. J Antibiot (Tokyo) 30: 349–370
Hurley LH, Petrusek R (1979) Proposed structure of the anthramycin-DNA adduct. Nature 282: 529–531
Hurley LH, Rokem JS, Petrusek RL (1980) Proposed structures of the pyrrolo(l,4)benzodiazepine antibiotic-deoxyribonucleic acid adducts. Biochem Pharmacol 29: 1307–1310
Kohn KW (1975) Anthramycin. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 3–11. Springer, Berlin Heidelberg New York
Kunimoto S, Masuda T, Kobayashi N, Hamada M, Naganawa H, Miyamoto M, Takeuchi T, Umezawa H (1980) Mazethramycin, a new member of anthramycin group antibiotics. J Antibiot (Tokyo) 33: 665–667
Maruyama IN, Suzuki H, Tanaka N (1978) Mechanism of action of neothramycin. I. The effect on macromolecular syntheses. J Antibiot (Tokyo) 31: 761–768
Maruyama IN, Tanaka N, Kondo S, Umezawa H (1979) Mechanism of action of neothramycin. II. Interaction with DNA. J Antibiot (Tokyo) 32: 928–934
Maruyama IN, Tanaka N, Kondo S, Umezawa H (1981 a) Fluorospectrometric studies on neothramycin and its reaction with DNA. J Antibiot (Tokyo) 34: 427–435
Maruyama IN, Tanaka N, Kondo S, Umezawa H (1981 b) Structure of a neothramycin-2-deoxyguan- osine adduct. Biochem Biophys Res Commun 98: 970–975
Miyamoto M, Kondo S, Naganawa H, Maeda K, Ohno M, Umezawa H (1977) Structure and synthesis of neothramycin. J Antibiot (Tokyo) 30: 340–343
Nishioka Y, Beppu T, Kohsaka M, Arima K (1972) Mode of action of tomaymycin. J Antibiot (Tokyo) 25: 660–667
Olmsted J III, Kearns DR (1977) Mechanism of ethidium fluorescence enhancement on binding to nucleic acids. Biochemistry 16: 3647–3654
Petrusek RL, Anderson GL, Garner TF, Fannin QL, Kaplan DJ, Zimmer SG, Hurley LH (1981) Pyrrolo(l,4)benzodiazepine antibiotics. Proposed structures and characteristics of the in vitro deoxyribonucleic acid adducts of anthramycin, tomaymycin, sibiromyin, and neothramycins A and B. Biochemistry 20: 1111–1119
Takeuchi T, Miyamoto M, Ishizuka M, Naganawa H, Kondo S, Hamada M, Umezawa H (1976) Neothramycins A and B, new antitumor antibiotics. J Antibiot (Tokyo) 29: 93–96
Waring M (1975) Ethidium and propidium. In: Corcoran JW, Hahn FE (eds) Antibiotics. Mechanism of action of antimicrobial and antitumor agents, vol III, pp 141–165. Springer, Berlin Heidelberg New York
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Tanaka, N. (1983). Neothramycin. In: Hahn, F.E. (eds) Modes and Mechanisms of Microbial Growth Inhibitors. Antibiotics, vol 6. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-68946-8_9
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DOI: https://doi.org/10.1007/978-3-642-68946-8_9
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